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Vacation rentals with a pool in Roosevelt Roads

Find and book unique homes with a pool on Airbnb

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Popular amenities for Roosevelt Roads rentals with a pool

House rentals with a pool

Top guest favorite
Home in Buena Vista
4.98 out of 5 average rating, 101 reviews

Amazing Infinity pool @Coqui Tropical House

Mary KathleenRating, 5 stars3 weeks ago
Our family loved our time at Luis & Ivette's place during our family vacation. Luis reached out to us on day one to ensure we had a smooth check-in, offer suggestions for local restaurants and activities and introduce us to the neighborhood. The home was lovely and well-equipped. The outdoor space is fantastic for relaxing, grilling, and playing with children. Our granddaughter swam in the pool every day and we really appreciated all the games and pool toys that were available for her use. A wonderful place to stay with plenty of room for families.
Guest favorite
Home in Trujillo Alto
4.88 out of 5 average rating, 26 reviews

Tropical Bliss House w/Pool

OrlandoRating, 5 stars1 week ago
Was a pleasure to be host from Jose Anthony, you can’t expect more everything is very accessible from the house to the restaurants to the highway to go anywhere you have to go is right in the middle of every place And the host was always attentive and very friendly and respectful offering more than just the beautiful home but also getting back to us every time we have a question with perfect suggestions and always very friendly available
Guest favorite
Home in Florida
4.94 out of 5 average rating, 108 reviews

Home for 9 with Pool and Solar Panels in Vieques!

IselaRating, 5 stars2 weeks ago
Beautiful place and wonderful host!
Superhost
Home in San Juan
4.92 out of 5 average rating, 130 reviews

Luxury Casa CA-LI-AD

DanielleRating, 5 stars1 week ago
We stayed at Casa CA-LI-AD with two families (4 adults, 3 kids under 8) and had an amazing experience. The listing is accurate—everything was as described, clean, and very family-friendly. It’s close to the airport, attractions, and a supermarket, which made things super convenient. During our stay, there was a rare island-wide blackout, and the host went above and beyond to make sure we had what we needed. The property’s generator made a huge difference and gave us peace of mind. Pro tip: when using Uber, enter Casa CA-LI-AD with the dashes—otherwise it might not show up in the app. As a fellow Airbnb superhost, I can honestly say this place is exceptionally well cared for. Highly recommend for families!
Guest favorite
Home in Ceiba
4.89 out of 5 average rating, 123 reviews

Coastal Getaway with Pool, Game Room & Ocean View

SharonRating, 5 stars4 weeks ago
Wonderful stay, beautiful place, can’t ask for anything more
Superhost
Home in Carolina
4.83 out of 5 average rating, 253 reviews

Nena’s place, Carolina PR w electric generator

LeeanneRating, 5 stars2 weeks ago
Great place and super clean!
Superhost
Home in Luquillo
4.68 out of 5 average rating, 44 reviews

La Casa Verde Luquillo (Green House Luquillo)

EmmaliaRating, 5 stars1 month ago
My friends and I stayed at this amazing Airbnb located right on Luquillo Beach. Seriously the most beautiful and quiet beach you will ever see. The pool was used basically everyday. It was nice to have a private area for us to use while we waited for other people to get ready for the day, or cool off after a long day of hiking and exploring the area. This air bnb is huge and honestly exceeded our expectations. The host was very responsive and friendly. There were even beach chairs and a beach cart for our use. He recommended lots of places and activites for us to do. CNote the Jazz bar is a must. Great location, we were able to either walk or drive everywhere. 25 minutes to the rain forest, 25 minutes to farajado. Highly recommend his place and location!
Guest favorite
Home in Punta Santiago
4.94 out of 5 average rating, 139 reviews

We are back! Puerto Rican paradise awaits you!

GraceRating, 5 stars1 month ago
Rick is a superior host, kind and communicative! The house was everything we could wish for. Steps to a beautiful beach, and a private pool, gorgeous views! Just perfect!

Condo rentals with a pool

Guest favorite
Condo in Cangrejo Arriba
4.86 out of 5 average rating, 254 reviews

Isla Verde-Alambique Beach Modern Condominium

AmberRating, 5 stars4 weeks ago
We had a wonderful stay at this charming home! It's in an ideal location—super close to the airport, which made our travel so much easier. The apartment was easy to find. The beach is just a short walk away and there are plenty of great restaurants nearby. The home itself was spotlessly clean and had a cozy, inviting atmosphere that made it feel like a true getaway. The balcony was nice. The check-in and check-out instructions were clear and easy to follow, making the whole process smooth and hassle-free. Highly recommend this place for anyone looking for a convenient and comfortable stay!
Superhost
Condo in Luquillo
4.95 out of 5 average rating, 133 reviews

Relax in modern ocean condo with amazing 270° view

KristinaRating, 5 stars3 weeks ago
Second time we have stayed at this incredible place. The wind, the ocean, the rainforest- it is so beautiful. The condo is comfortable and AC in the bedrooms works great. We swam in the ocean and also enjoyed the pool at the condo! We love this place.
Guest favorite
Condo in Naguabo
4.9 out of 5 average rating, 166 reviews

Ocean View Penthouse Condo with A/C in every Room

ERating, 5 stars1 week ago
Excellent location, very quiet place, very comfortable for the family and for kids, beautiful view, beautiful surroundings, with a beach, a pool, a basketball and tennis court, too and a 10 minute walking distance from the "Malecón de Naguabo" where there are a lot of places to eat and very delicious. Hosts very responsive and proactive to help with everything! Thanks Diane and Luis for sharing this blessed place with us!
Superhost
Condo in Fajardo
4.79 out of 5 average rating, 112 reviews

Lovely Ocean View Apartment

AngelaRating, 5 stars2 weeks ago
This unit is exactly as pictured with plenty of space, comfy beds and linens, a stocked kitchen and beautiful view. Cold AC in both bedrooms, but not in the living room. Secure building with elevators. Slightly dated but clean and well kept. Our only complaint was the location is next to a very busy marina, there is often noise and loud music from the boats and the restaurant next door but it stopped by midnight or so. Overall we were very pleased and would definitely stay here again!
Guest favorite
Condo in PR
4.83 out of 5 average rating, 179 reviews

Perfect Location 3bd2ba CondoVacation/Business

lillieRating, 5 stars2 weeks ago
Brad & Juanita condo was just right bed was conftoble water pressure was good The location was perfect, with many beaches nearby and We enjoyed exploring the area and found plenty of great dining options nearby. , our experience was amazing. We would highly recommend
Guest favorite
Condo in Río Grande
4.86 out of 5 average rating, 109 reviews

Beachfront Top Floor Condo next to Wyndham Hotel

MaryRating, 5 stars2 weeks ago
This was our second time staying here and we loved it again! It fits our family of four so nicely. We can easily make meals and hang out on the balcony looking at the beautiful ocean or walk down and be right on the beach in minutes. We even reached out once to Tom noticing something was missing from the kitchen and he went to the store and brought it to us the very next day. Totally not expected and way above and beyond! We hope to come back next year and would definitely stay again if it is available.
Guest favorite
Condo in Zarzal
4.95 out of 5 average rating, 220 reviews

Beachfront Paradise - 2 BR/BA Condo near El Yunque

MichaelRating, 5 stars3 weeks ago
Our group of 3 had a lovely stay. Host was helpful and the place was clean and comfortable. Having a pool and beach amenities (chairs, towels, boogie boards) was a huge plus along with the welcome snacks. The beach out front was not great for swimming (we were also there during a windy period so that made it harder), but it’s an easy drive to some other more protected spots. Nice restaurants are a short drive, and it’s easy to get to the rain forest for some cool hikes and adventures. Overall, we were very happy with the condo.
Guest favorite
Condo in Vieques
4.88 out of 5 average rating, 117 reviews

My paradise to you @ Aquatika

EmmaRating, 5 stars2 weeks ago
We absolutely enjoyed our stay! The pictures were good but the apartment looks better in person than in the pictures. Zenen and Wanda were very responsive and easy to get ahold of! We had a minor issue with the ac(ended up just being that the batteries in the ac remote needed to be changed) we contacted them and they fixed the issue within the hour! We appreciated how fast they responded to us. You can tell they actually care. Aquátika also is a lovely place. The landscaping & the pool areas were beautiful and clean. Aquatika also has 24/7 security & is gated so we felt extra safe! I definitely would recommend staying booking with Zenen and Wanda.

Quick stats about vacation rentals with a pool in Roosevelt Roads

  • Total rentals

    90 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 before taxes and fees

  • Total number of reviews

    3.8K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

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